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Rapid fabrication of zwitterionic sulfobetaine vinylimidazole-based monoliths via photoinitiated copolymerization for hydrophilic interaction chromatography

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Journal of Pharmaceutical Analysis 2022年第5期12卷 783-790页

作者： Qiqin Wang Lingjue Sun Huihui Wu Ning Deng Xianglong Zhao Jingwei Zhou Tingting Zhang Hai Han Zhengjin Jiang Institute of Pharmaceutical Analysis College of PharmacyJinan UniversityGuangzhou510632China Anhui Prevention and Treatment Center for Occupational Disease Anhui No.2 Provincial People's HospitalHefei230041China Key Laboratory of Environment-Friendly Chemistry and Application of Ministry of Education Lab of BiochemistryCollege of ChemistryXiangtan UniversityXiangtanHunan411105China Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine&New Drug Research Jinan UniversityGuangzhou510632China

Zwitterionic sulfobetaine-based monolithic stationary phases have attracted increasing attention for their use in hydrophilic interaction chromatography.In this study,a novel hydrophilic polymeric monolith was fabricated through photo-initiated copolymerization of 3-(3-vinyl-1-imidazolio)-1-propanesulfonate(SBVI)with pentaerythritol triacrylate using methanol and tetrahydrofuran as the porogenic system.Notably,the duration for the preparation of this novel monolith was as little as 5 min,which was significantly shorter than that required for previously reported sulfobetaine-based monoliths prepared via conventional thermally initiated copolymerization.Moreover,these monoliths showed good morphology,permeability,porosity(62.4%),mechanical strength(over 15 MPa),column efficiency(51,230 plates/m),and reproducibility(relative standard deviations for all analytes were lower than 4.6%).Mechanistic studies indicated that strong hydrophilic and negative electrostatic interactions might be responsible for the retention of polar analytes on the zwitterionic SBVI-based monolith.In particular,the resulting monolith exhibited good anti-protein adhesion ability and low nonspecific protein adsorption.These excellent features seem to favor its application in bioanalysis.Therefore,the novel zwitterionic sulfobetaine-based monolith was successfully employed for the highly selective separation of small bioactive compounds and the efficient enrichment of N-glycopeptides from complex samples.In this study,we prepared a novel zwitterionic sulfobetaine-based monolith with good performance and developed a simpler and faster method for preparation of zwitterionic monoliths.

关键词： Zwitterionic monolith Sulfobetaine Photo-initiated copolymerization hydrophilic interaction chromatography Complex sample

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A novel hydrophilic polystyrene-based beads for hydrophilic interaction chromatography by surface-initiated atom transfer radical polymerization

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Chinese Chemical Letters 2011年第2期22卷 245-248页

作者： Xiao Jun Dai Yuan He Yin Mao Wei Bo Lin Gong Key Laboratory of Synthetic and Natural Function Molecule Chemistry of Ministry of Education College of Chemistry & Material Science Northwest University Xi'an 710069 China Key Laboratory of Energy & Chemical Engineering Ningxia University Yinchuan 750021 China Received 4 June 2010

A one-step procedure to hydrophilize monodisperse poly（chloromethyl-styrene-co-divinylbenzene） beads has been presented with 2-hydroxy-3-[4-（hydroxymethyl）-1H-1,2,3-triazol-1-yl]propy1 2-methylacrylate（HTMA） as monomer by surface-initiated atom transfer radical polymerization（SI-ATRP）.The length of the grafted poly（HTMA） chain was varied via controlling the ratio of HTMA to initiator on the surface of the beads.Using these grafted beads as the stationary phase in hydrophilic interaction chromatography,good separation was obtained for nucleosides in the mobile phase of acetonitrile-water.It was also found that the retention time and selectivity of solutes showed a positive relationship with the length of the grafted poly（HTMA） chain.

关键词： hydrophilic interaction chromatography Polystyrene-based beads Surface-initiated atom transfer radical polymerization 1,2,3-Triazole

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Simultaneous determination of 15 nucleosides and nucleobases in natural Cordyceps by hydrophilic interaction chromatography- electrospray ionization tandem mass spectrometry

Simultaneous determination of 15 nucleosides and nucleobases...

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中华中医药学会中药分析分会第五届学术交流会

作者： Xiao Wang~(1,2),Hengqiang Zhao~1,Hongmei Li~2,Bin Yang~2,Hongjun Yang~2,Luqi Huang~(2*) (1 Shandong Analysis and Test Center,Shandong Academy of Sciences,Jinan 250014,China 2 Institute of Chinese Material Medical,China Academy of Chinese Medical Sciences,16 Dongzhimennei Street,Beijing 100700, China)

Cordyceps sinensis has been widely used as traditional Chinese medicines(TCM) in China.To date,nucleosides are believed to be the bioactive components in Cordyceps.Therefore,a specific and sensitive analysis method of these compounds is essential for the quality control of Cordyceps.hydrophilic interaction liquid chromatography(HILIC) was proposed for the separation of highly hydrophilic compounds by Alpert in 1990,which was characterized by polar stationary phases and aqueous-organic mobile phases.Tandem mass spectrometry could provides low limits of detection and high selectivity capabilities, so the HILIC-ESI-MS/MS method would be more suitable for the quantitative analysis of high polar compound in complex matrix.In this study,a hydrophilic interaction chromatography(HILIC) and electrospray ionization tandem mass spectrometry(ESI -MS/MS) method was developed for the identification and quantification of 15 nucleosides and nucleobases namely thymine,uracil, thymidine,2’-deoxyuridine,cordycepin,uridine,hypoxanthine,adenine,adenosine,xanthine,inosine,cytosine,guanine, cytidine,guanosine in natural Cordyceps.The separation was achieved on a Waters Xbridge Amide column(250x4.6 mm I.D.,3.5 um) and gradient elution using a solution of acetonitrile and buffer(0.20%acetic acid and 10 mmol/L ammonium acetate) as the mobile phase at a flow rate of 0.8 mL/min.Identification of the 16 target nucleosides and nucleobases was based on retention time, UV spectra,mass measurements of the protonated molecules([M+H]) and main fragment ions(ESI-MS/MS).Quantitative analysis of investigated compounds were performed using time programmed selective ion monitoring(SIM) or multiple reaction monitoring (MRM) in positive ion mode under optimized mass conditions.All calibration curves showed good linearity(r > 0.9951) within the test ranges.The overall intra- and inter-day RSD ranged from 2.45 to 5.23%and from 3.29 to 6.73%,respectively.The LOD were in the range of 0.15-10.00 ng/mL,respectively.The recoveries of the samples were in the ran

关键词： Cordyceps nucleosides and nucleobases hydrophilic interaction chromatography electrospray ionization tandem mass spectrometry

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Quantitative analysis of therapeutic mAb glycoforms by hydrophilic interaction chromatography enrichment and parallel reaction monitoring

Quantitative analysis of therapeutic mAb glycoforms by hydro...

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中国化学会第30届学术年会-第二十三分会：复杂样品分离...

作者： Yuting Cong Lianghai Hu School of Life Sciences Jilin University

Monoclonal antibodies（mAbs）,are one of the most important protein drugs have attracted increasing attention.However,the pharmacokinetics of mAbs has not been fully investigated due to the complexity of protein drugs.Traditonal immuno-based approaches can not recognize the proteoforms of mAbs due to the long development cycles,prohibitive cost and interactions between different proteins.Therefore,reliable qualitative and quantitative analysis of the proteoforms of mAbs in biological samples is of crucial importance.Herein,a novel method was developed for absolute quantitation of mAbs and their glycoforms in complex biological samples such as serum and tissues.With the combination of HILIC enrichment and parallel reaction monitoring by high resolution mass spectrometry,most of the glycoforms can be accurately quantified at the fmol level through the use of the model mAb of bevacizumab.More importantly,the structural confirmation can be achieved simultaneously without the need for additional experiments.This strategy can be readily applied to the pharmacokinetic study of glycosylation modification and biomarker discovery for clinical applications.

关键词： Proteomics hydrophilic interaction chromatography therapeutic monoclonal antibody glycosylation parallel reaction monitoring

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Application of hydrophilic interaction chromatography in natural product analysis

Application of hydrophilic interaction chromatography in nat...

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中华中医药学会第七次中药分析学术交流会

作者： Yan Gao Yi Luo Ru-Feng Wang Bin Liu School of Chinese Medicine Beijing University of Chinese Medicine

Recently,the hydrophilic interaction chromatography(HILIC) developed rapidly for highly polar compounds with good separation and have drawn more highly focused on natural products isolation areas.In this paper,to describe HILIC mobile phase、 stationary phase and its application in NPs analysis,for the purpose of providing a reference for the polar compounds separation and the NPs application.

关键词： hydrophilic interaction chromatography natural products separation highly polar compounds

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Rapid determination of amino acids without derivatization using hydrophilic interaction ultra-high performance liquid chromatography coupled with triple quadrupole mass spectrometry

Rapid determination of amino acids without derivatization us...

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中华中医药学会中药分析分会第五届学术交流会

作者： Sheng Guo,Jin-ao Duan~*,Dawei Qian,Yuping Tang,Yefei Qian,Dawei Wu,Shulan Su,Erxin Shang Jiangsu Key Laboratory for High Technology Research of TCM Formulae,Nanjing University of Chinese Medicine,Nanjing 210046,PR. China

A novel hydrophilic interaction liquid chromatography coupled with tandem mass spectrometry (HIL1C-MS/MS) method was developed for the simultaneous determination of 23 free amino acids without derivatization.The method was performed on an ultra-high performance liquid chromatography(UHPLC) separation system coupled with electrospray ionization mass spectrometry on a triple quadrupole mass spectrometer (TQ-MS),operating in positive ionization mode.Sufficient separation of the 23 underivatized amino acids was achieved on an Acquity BEH Amide column(2.1 mm×100 mm,1.7μm) in a single run of 12 min at a flow rate of 0.4 mL min.The limits of detection were in the range from 0.17 to 77.75 ng mL.All the analytes were quantified directly from biological extracts without any kind of derivatization,which avoided the laborious and time-consuming of derivatization procedures used by the traditional method.Also,the more polar compounds were separated without utilization of perfluorinated acids as ion-pairing reagents which was not suggested for ESI source. Then,the method was applied for the analysis of the free amino acids in 46 batches of Ziziphus jujuba fruits which comprised 39 cultivars from 26 cultivation regions.Multivariate statistical analysis was also used to investigate the differences in free amino acid profiles among the samples.This study showed that HILIC-UHPLC-TQ-MS is an effective technique to analyze underivatized amino acids in the biological samples.

关键词： Amino acid Ziziphus jujuba hydrophilic interaction chromatography Ultra-high performance liquid chromatography Triple quadrupole mass spectrometry

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Challenges in Analysis of hydrophilic Metabolites Using chromatography Coupled with Mass Spectrometry

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Journal of Analysis and Testing 2020年第3期4卷 140-162页

作者： Qingyu Hu Huiru Tang Yulan Wang CAS Key Laboratory of Magnetic Resonance in Biological Systems State Key Laboratory of Magnetic Resonance and Atomic and Molecular PhysicsNational Centre for Magnetic Resonance in WuhanWuhan Institute of Physics and MathematicsInnovation Academy for Precision Measurement Science and TechnologyChinese Academy of Sciences(CAS)Wuhan 430071People’s Republic of China University of Chinese Academy of Sciences Beijing 10049People’s Republic of China State Key Laboratory of Genetic Engineering Zhongshan Hospital and School of Life SciencesLaboratory of Metabonomics and Systems BiologyHuman Phenome InstituteFudan UniversityShanghai 200433People’s Republic of China Singapore Phenome Center Lee Kong Chian School of MedicineNanyang Technological UniversitySingapore 639798Singapore

hydrophilic metabolites play important roles in cellular energy metabolism,signal transduction,immunity.However,there are challenges in both identification and quantification of the hydrophilic metabolites due to their weak interactions with C18-reversed-phase liquid chromatography(RPLC),leading to poor retention of hydrophilic metabolites on the columns.Many strategies have been put forward to increase the retention behavior of hydrophilic metabolites in the RPLC system.Non-derivatization methods are mainly focused on the development of new chromatographic techniques with different separation mechanisms,such as capillary electrophoresis,ion-pairing RPLC etc.Derivatization methods improve the hydrophobicity of metabolites and can enhance the MS response.This review mainly focused on the illustration of challenges of LCMS in the analysis of hydrophilic metabolomics field,and summarized the non-derivatization and derivatization strategies,with the intention of providing multiple choices for analysis of hydrophilic metabolites.

关键词： hydrophilic metabolites hydrophilic interaction chromatography Ion-pairing reversed-phase liquid chromatography Ion chromatography Capillary electrophoresis Derivatization

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Sensitive and accurate determination of trehalose-6-phosphate in plant tissues by chemical derivatization combined with hydrophilic interaction chromatographytandem mass sp ectrometry

Sensitive and accurate determination of trehalose-6-phosphat...

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2018年中国质谱学术大会（CMSC2018）

作者： Xiao-Tong Luo Bao-Dong Cai Han-Peng Jiang Hua-Ming Xiao Bi-Feng Yuan Yu-Qi Feng Key Laboratory of Analytical Chemistry for Biology and Medicine (Ministry of Education) Department of ChemistryWuhan University

Trehalose-6-phosphate(T6 P), the precursor of trehalose in the biosynthetic pathway, is an important signaling metabolite that is involved in many physiological processes [1-2]. However, it is not always clear to what extent it accelerates growth or with what mechanism it acts as a metabolic regulator [3]. Therefore, quantification of T6 P in plants will be beneficial to find out the mechanism. But it is still a challenge to chromatographically separate T6 P and relative sugar phosphates with high resolution and detect them with high sensitivity. In the current study, we developed a method for effective separation and sensitive determination of endogenous T6 P and related sugar phosphates in plant tissues by chemical derivatization combined with hydrophilic interaction chromatographytandem mass spectrometry(CD-HILIC LC-MS/MS). Two pairs of isomers(T6 P and sucrose-6-phosphate;glucose-1-phosphate and glucose-6-phosphate) after chemical derivatization could be well separated on a HILIC LC column;the ionization efficiency and MS fragmentation behavior of T6 P and related phosphates was improved. Therefore, the limit of detection(LOD) for the analytes we investigated ranged from 0.1 to 0.6 ng mL-1. Good linearity of the proposed method was obtained with correlation coefficients(r) ranging from 0.9935 to 0.9999. The recoveries were between 91.5% and 108.5%, and the related standard deviations(RSDs) were 1.1%-9.7%. Finally, the developed method was successfully applied to the analysis of endogenous T6 P and related sugar phosphates in small amount of plant tissues including 1 mg FW Oryza sativa shoot, 5 mg FW Oryza sativa root and 10 mg FW Arabidopsis thaliana shoot with the concentration ranging from 0.7 to 47.5 μg g-1 FW.

关键词： Sugar phosphate Chemical derivatization Mass spectrometry hydrophilic interaction chromatography

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Underivatized amino acids analysis based on ultra performance liquid chromatography coupled to Q-TOF mass spectrometry（UPLC/Q-TOF MS）

Underivatized amino acids analysis based on ultra performanc...

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30th International Symposium on Capillary chromatography、4th GC×GC Symposium、16th National Symposium and Exhibition on chromatography,i.e. 1st Dalian International Symposium and Exhibition on chromatography

作者： Jing Chen Peiyuan Yin Xin Lu Guowang Xu~* National Chromatographic Research and Analysis Center Institute of Chemical Physics the Chinese Academy of Sciences Dalian 116023 China

＜正＞Amino acids play an important role in the metabolism of the human organism.Abnormal levels of amino acids suggest that certain metabolism pathway has been disrupted.For instance,phenyl ketonuria will probably ap... 详细信息

关键词： Amino Acid UPLC-MS hydrophilic interaction chromatography

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